II. Indications

  1. Serious Gram Negative Bacterial infection
  2. Use alone or in combination with Aminoglycosides

III. Preparations

  1. Alpha carboxy Penicillin
    1. Carbenicillin
    2. Ticarcillin (Ticar)
    3. Ticarcillin clavulanate (Timentin)
  2. Acylamino-Penicillin
    1. Mezlocillin (Mezlin)
    2. Piperacillin (Pipracil)
    3. Piperacillin tazobactam (Zosyn)

IV. Mechanism

  1. Similar to Natural Penicillins
  2. Greater penetration through Gram Negative membrane
  3. High affinity for Penicillin binding proteins
  4. Beta lactamase resistance with Clavulanate, Tazobactam

V. Mechanism: Bacterial Resistance

  1. Beta lactamase (except with Clavulanate or Tazobactam)
  2. Alteration of Penicillin binding proteins (Pseudomonas)

VI. Dosing: Parenteral

  1. Ticarcillin Clavulanate (Timentin)
    1. Adult: 3.1 g IV q4-6h
    2. Child: 50 mg/kg up to 3.1 g IV q4-6 hours
  2. Piperacillin Tazobactam (Zosyn)
    1. Adult: 3.375 g IV q6 hours

VII. Adverse Effects

  1. Many side effects in addition to Natural Penicillins
  2. High Sodium load (Carbenicillin)
  3. Platelet Dysfunction

VIII. Activity Spectrum

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Ontology: Carbenicillin (C0006976)

Definition (NCI) A broad-spectrum, semi-synthetic penicillin antibiotic with bactericidal and beta-lactamase resistant activity. Carbenicillin acylates the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation prevents the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This leads to incomplete bacterial cell wall synthesis and eventually causes cell lysis.
Definition (MSH) Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D002228
SnomedCT 34731007, 372713001
LNC LP16062-9, MTHU007966
English Carbenicillin, Carboxybenzyl Penicillin, Penicillin, Carboxybenzyl, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxyphenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, carbenicillin, Carbenicillin [Chemical/Ingredient], Carbenicillin (product), Carbenicillin (substance), CARBENICILLIN
Swedish Karbenicillin
Czech karbenicilin
Finnish Karbenisilliini
Russian KARBOKSIBENZILPENITSILLIN, KARBENITSILLIN, КАРБЕНИЦИЛЛИН, КАРБОКСИБЕНЗИЛПЕНИЦИЛЛИН
Japanese カルベニシリン, カルボキシベンジルペニシリン, カルベニシリンナトリウム
Croatian CARBENICILLIN
Polish Karbenicylina
Spanish Carboxibencilpenicilina, carbenicilina (producto), carbenicilina (sustancia), carbenicilina, Carbenicilina, Carboxibencil Penicilina
French Carbénicilline
German Carbenicillin, Carboxybenzylpenizillin
Italian Carbenicillina
Portuguese Carbenicilina, Carboxibenzilpenicilina

Ontology: Piperacillin (C0031955)

Definition (NCI) A broad-spectrum semisynthetic, ampicillin-derived ureidopenicillin antibiotic. Piperacillin binds to penicillin binding proteins (PBP), the enzymes that catalyze the synthesis of peptidoglycan, a critical component of the bacterial cell wall. This blockade leads to the interruption of cell wall synthesis, consequently, leading to bacterial cell growth inhibition and cell lysis.
Definition (MSH) Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D010878
SnomedCT 372836004, 74575000
LNC LP16256-7, MTHU008471
English Pipercillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-, piperacillin, piperacillin (medication), Piperacillin [Chemical/Ingredient], pipercillin, (2S,5R,6R)-6-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid Monohydrate, PIPERACILLIN, Piperacillin (product), Piperacillin (substance), Piperacillin
Swedish Piperacillin
Czech piperacilin
Finnish Piperasilliini
Russian PIPERATSILLIN, ПИПЕРАЦИЛЛИН
Japanese ピシリアント, プランジン, ホモスリン, ペンマリン, ペントシリン, ピペラシリンナトリウム, ピペユンシン, アルカベミン, ピペラシリン
Italian Pipercillina, Piperacillina
Croatian PIPERACILIN
Polish Piperacylina
Spanish piperacilina (producto), piperacilina (sustancia), piperacilina, Piperacilina
French Pipéracilline
German Piperacillin
Portuguese Piperacilina

Ontology: Ticarcillin (C0040193)

Definition (NCI) A broad-spectrum, semi-synthetic penicillin antibiotic with bactericidal activity. Similar to carbenicillin in action, ticarcillin inactivates the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation prevents the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This leads to incomplete bacterial cell wall synthesis and eventually causes cell lysis.
Definition (MSH) An antibiotic derived from penicillin similar to CARBENICILLIN in action.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D013982
SnomedCT 1148001, 372577006
LNC LP16291-4, MTHU008492
English Ticarcillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxy-3-thienylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-, ticarcillin, Ticarcillin [Chemical/Ingredient], ticarcillin (medication), TICARCILLIN, Ticarcillin (product), Ticarcillin (substance), Ticarcillin, NOS
Swedish Ticarcillin
Czech tikarcilin
Finnish Tikarsilliini
Russian TIKARTSILLIN, BRL 2288, ТИКАРЦИЛЛИН
Japanese チカルシリン, チカルシリンナトリウム
Polish Tikarcylina
Spanish ticarcilina (producto), ticarcilina (sustancia), ticarcilina, Ticarcilina
French Ticarcilline
German Ticarcillin
Italian Ticarcillina
Portuguese Ticarcilina

Ontology: Timentin (C0076686)

Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH C043215
English Timentin, Timentin ADD-Vantage, timentin